Wavelength conversion luminescent resin composition, method for producing wavelength conversion luminescent resin composition, wavelength conversion member, and light-emitting element

ABSTRACT

An object of the present invention is to provide a wavelength conversion luminescent resin composition that exhibits a high quantum yield, a wavelength conversion member, and a light-emitting element; as well as a method for producing the wavelength conversion luminescent resin composition that exhibits a high quantum yield. The present invention provides a wavelength conversion luminescent resin composition that contains at least one compound represented by Formula (1) and a resin. 
     
       
         
         
             
             
         
       
     
     The substituents in the formula are as defined in the present specification.

CROSS-REFERENCE TO RELATED APPLICATIONS

This application is a Continuation of PCT International Application No.PCT/JP2017/045448 filed on Dec. 19, 2017, which claims priority under 35U.S.C § 119(a) to Japanese Patent Application No. 2016-245318 filed onDec. 19, 2016. Each of the above application(s) is hereby expresslyincorporated by reference, in its entirety, into the presentapplication.

BACKGROUND OF THE INVENTION 1. Field of the Invention

The present invention relates to a wavelength conversion luminescentresin composition containing a compound having a specific structure. Thepresent invention further relates to a wavelength conversion memberincluding a wavelength conversion luminescent resin composition, alight-emitting element, and a method for producing a wavelengthconversion luminescent resin composition.

2. Description of the Related Art

Currently, an incandescent bulb, a fluorescent lamp, a light emittingdiode (LED), electroluminescence, and the like are used as alight-emitting element. For example, light generated from anincandescent bulb and a fluorescent lamp is light by heat or discharge,and there is a fundamental problem that the life of a heat source ordischarge source is short, so that the life of the incandescent bulb orfluorescent lamp as the light-emitting element is limited. On the otherhand, the light radiation of a light emitting diode (LED) isluminescence due to inherent properties of a semiconductor, and LED isexpected to achieve a longer life. As described above, various methodsare used as the light emission method, and the characteristicimprovement thereof is still being continued now.

It is known that light emitted from a light-emitting element is dimmedby a wavelength conversion material (also referred to as a colorconversion material) containing an organic coloring agent. Such awavelength conversion material is used for lighting applications anddisplay applications. A light source for lighting is particularlyrequired to have properties of how to resemble natural light, such ascolor rendering properties. In addition, a light source for display isrequired to have color reproducibility.

As the color conversion material, for example, JP2011-241160A disclosesa color conversion material including a pyrromethene boron complexcompound. In addition, WO2015/056779A discloses a resin compositioncontaining a near infrared fluorescent coloring agent such aspyrromethene boron complex and a resin.

SUMMARY OF THE INVENTION

The color conversion material disclosed in JP2011-241160A has a problemthat the quantum yield decreases due to aggregation, resulting from thestructure of the pyrromethene boron complex compound to be used. Theresin composition disclosed in WO2015/056779A has a problem that thewavelength conversion material is insufficient in luminance with longwave light emission and low in quantum yield.

An object of the present invention is to provide a wavelength conversionluminescent resin composition which exhibits a high quantum yield, awavelength conversion member, and a light-emitting element. Anotherobject of the present invention is to provide a method for producing thewavelength conversion luminescent resin composition which exhibits ahigh quantum yield.

As a result of extensive studies to achieve the foregoing objects, thepresent inventors have found that it is possible to produce a wavelengthconversion luminescent resin composition exhibiting a high quantum yieldby producing a wavelength conversion luminescent resin composition usinga compound having a specific structure and a resin. The presentinvention has been completed based on these findings.

That is, according to the present invention, the following inventionsare provided.

[1] A wavelength conversion luminescent resin composition, comprising:

at least one compound represented by Formula (1); and

a resin,

in Formula (1), Y¹ and Y² each independently represent a halogen atom,an alkyl group, an aryl group, a hydroxy group, an alkoxy group, or anaryloxy group, each of which may have a substituent, and Y¹ and Y² maybe linked to each other to form a ring; R³ represents a hydrogen atom,an alkyl group, an aryl group, a heterocyclic group, an ethenyl group,an ethynyl group, or an acyl group, each of which may have asubstituent; Ar³ and Ar⁴ each independently represent an aryl group,each of which may have a substituent; and R⁴ to R¹¹ each independentlyrepresent a hydrogen atom, a halogen atom, an alkyl group, an arylgroup, a heterocyclic group, an ethenyl group, an ethynyl group, an acylgroup, an alkoxy group, an aryloxy group, an alkylthio group, anarylthio group, or an amino group, each of which may have a substituent,and at least one of R⁴, . . . , or R¹¹ represents a substituentrepresented by Formula (2) or Formula (3),

in Formula (2), R²⁰¹ represents a halogen atom, an alkyl group, an arylgroup, a heterocyclic group, an ethenyl group, an ethynyl group, an acylgroup, a silyl group, an alkoxy group, an aryloxy group, an alkylthiogroup, an arylthio group, or an amino group, each of which may have asubstituent; and Q represents an aromatic ring which may have asubstituent,

in Formula (3), R¹⁰¹ represents an alkyl group, an aryl group, aheterocyclic group, an ethenyl group, an ethynyl group, or an acylgroup, each of which may have a substituent; Ar¹⁰¹ represents an arylgroup or a heterocyclic group, each of which may have a substituent; andAr¹⁰¹ and R²⁰¹ may be linked to each other to form a ring.

[2] The wavelength conversion luminescent resin composition according to[1], in which at least one of R⁴, . . . , or R¹¹ represents asubstituent represented by Formula (5),

in Formula (5), R²⁰¹ to R²⁰⁵ each represent a hydrogen atom, a halogenatom, an alkyl group, an aryl group, a heterocyclic group, an ethenylgroup, an ethynyl group, an acyl group, a silyl group, an alkoxy group,an aryloxy group, an alkylthio group, an arylthio group, or an aminogroup, and at least one of R²⁰¹ or R²⁰⁵ is a group other than a hydrogenatom; and R²⁰¹ and R²⁰² may be linked to each other to form a ring, R²⁰²and R²⁰³ may be linked to each other to form a ring, R²⁰³ and R²⁰⁴ maybe linked to each other to form a ring, and R²⁰⁴ and R²⁰⁵ may be linkedto each other to form a ring.

[3] The wavelength conversion luminescent resin composition according to[1] or [2], in which Ar³ and Ar⁴ are each independently a substituentrepresented by Formula (2),

in Formula (2), R²⁰¹ represents a halogen atom, an alkyl group, an arylgroup, a heterocyclic group, an ethenyl group, an ethynyl group, an acylgroup, a silyl group, an alkoxy group, an aryloxy group, an alkylthiogroup, an arylthio group, or an amino group, each of which may have asubstituent; and Q represents an aromatic ring which may have asubstituent.

[4] The wavelength conversion luminescent resin composition according to[1] or [2], in which Ar³ and Ar⁴ are each independently a substituentrepresented by Formula (5),

in Formula (5), R²⁰¹ to R²⁰⁵ each represent a hydrogen atom, a halogenatom, an alkyl group, an aryl group, a heterocyclic group, an ethenylgroup, an ethynyl group, an acyl group, a silyl group, an alkoxy group,an aryloxy group, an alkylthio group, an arylthio group, or an aminogroup, and at least one of R²⁰¹ or R²⁰⁵ is a group other than a hydrogenatom; and R²⁰¹ and R²⁰² may be linked to each other to form a ring, R²⁰²and R²⁰³ may be linked to each other to form a ring, R²⁰³ and R²⁰⁴ maybe linked to each other to form a ring, and R²⁰⁴ and R²⁰⁵ may be linkedto each other to form a ring.

[5] A wavelength conversion member comprising the wavelength conversionluminescent resin composition according to any one of [1] to [4].

[6] A light-emitting element comprising the wavelength conversion memberaccording to [5].

[7] A method for producing a wavelength conversion luminescent resincomposition, comprising:

a step of drying a solution containing at least one compound representedby Formula (1) and a resin in a solvent,

in Formula (1), Y¹ and Y² each independently represent a halogen atom,an alkyl group, an aryl group, a hydroxy group, an alkoxy group, or anaryloxy group, each of which may have a substituent, and Y¹ and Y² maybe linked to each other to form a ring; R³ represents a hydrogen atom,an alkyl group, an aryl group, a heterocyclic group, an ethenyl group,an ethynyl group, or an acyl group, each of which may have asubstituent; Ar³ and Ar⁴ each independently represent an aryl group,each of which may have a substituent; and R⁴ to R¹¹ each independentlyrepresent a hydrogen atom, a halogen atom, an alkyl group, an arylgroup, a heterocyclic group, an ethenyl group, an ethynyl group, an acylgroup, an alkoxy group, an aryloxy group, an alkylthio group, anarylthio group, or an amino group, each of which may have a substituent,and at least one of R⁴, . . . , or R¹¹ represents a substituentrepresented by Formula (2) or Formula (3),

in Formula (2), R²⁰⁰ represents a halogen atom, an alkyl group, an arylgroup, a heterocyclic group, an ethenyl group, an ethynyl group, an acylgroup, a silyl group, an alkoxy group, an aryloxy group, an alkylthiogroup, an arylthio group, or an amino group, each of which may have asubstituent; and Q represents an aromatic ring which may have asubstituent,

in Formula (3), R¹⁰¹ represents an alkyl group, an aryl group, aheterocyclic group, an ethenyl group, an ethynyl group, or an acylgroup, each of which may have a substituent; Ar¹⁰¹ represents an arylgroup or a heterocyclic group, each of which may have a substituent; andAr¹⁰¹ and R²⁰¹ may be linked to each other to form a ring.

[8] A method for producing a wavelength conversion luminescent resincomposition, comprising:

a step of curing a composition containing at least one compoundrepresented by Formula (1) and a monomer and/or a polymerizationprecursor,

in Formula (1), Y¹ and Y² each independently represent a halogen atom,an alkyl group, an aryl group, a hydroxy group, an alkoxy group, or anaryloxy group, each of which may have a substituent, and Y¹ and Y² maybe linked to each other to form a ring; R³ represents a hydrogen atom,an alkyl group, an aryl group, a heterocyclic group, an ethenyl group,an ethynyl group, or an acyl group, each of which may have asubstituent; Ar³ and Ar⁴ each independently represent an aryl group,each of which may have a substituent; and R⁴ to R¹¹ each independentlyrepresent a hydrogen atom, a halogen atom, an alkyl group, an arylgroup, a heterocyclic group, an ethenyl group, an ethynyl group, an acylgroup, an alkoxy group, an aryloxy group, an alkylthio group, anarylthio group, or an amino group, each of which may have a substituent,and at least one of R⁴, . . . , or R¹¹ represents a substituentrepresented by Formula (2) or Formula (3),

in Formula (2), R²⁰¹ represents a halogen atom, an alkyl group, an arylgroup, a heterocyclic group, an ethenyl group, an ethynyl group, an acylgroup, a silyl group, an alkoxy group, an aryloxy group, an alkylthiogroup, an arylthio group, or an amino group, each of which may have asubstituent; and Q represents an aromatic ring which may have asubstituent,

in Formula (3), R¹⁰¹ represents an alkyl group, an aryl group, aheterocyclic group, an ethenyl group, an ethynyl group, or an acylgroup, each of which may have a substituent; Ar¹⁰¹ represents an arylgroup or a heterocyclic group, each of which may have a substituent; andAr¹⁰¹ and R²⁰¹ may be linked to each other to form a ring.

[9] A method for producing a wavelength conversion luminescent resincomposition, comprising:

a step of melting a composition containing at least one compoundrepresented by Formula (1) and a resin,

in Formula (1), Y¹ and Y² each independently represent a halogen atom,an alkyl group, an aryl group, a hydroxy group, an alkoxy group, or anaryloxy group, each of which may have a substituent, and Y¹ and Y² maybe linked to each other to form a ring; R³ represents a hydrogen atom,an alkyl group, an aryl group, a heterocyclic group, an ethenyl group,an ethynyl group, or an acyl group, each of which may have asubstituent; Ar³ and Ar⁴ each independently represent an aryl group,each of which may have a substituent; and R⁴ to R¹¹ each independentlyrepresent a hydrogen atom, a halogen atom, an alkyl group, an arylgroup, a heterocyclic group, an ethenyl group, an ethynyl group, an acylgroup, an alkoxy group, an aryloxy group, an alkylthio group, anarylthio group, or an amino group, each of which may have a substituent,and at least one of R⁴, . . . , or R¹¹ represents a substituentrepresented by Formula (2) or Formula (3),

in Formula (2), R²⁰¹ represents a halogen atom, an alkyl group, an arylgroup, a heterocyclic group, an ethenyl group, an ethynyl group, an acylgroup, a silyl group, an alkoxy group, an aryloxy group, an alkylthiogroup, an arylthio group, or an amino group, each of which may have asubstituent; and Q represents an aromatic ring which may have asubstituent,

in Formula (3), R¹⁰¹ represents an alkyl group, an aryl group, aheterocyclic group, an ethenyl group, an ethynyl group, or an acylgroup, each of which may have a substituent; Ar¹⁰¹ represents an arylgroup or a heterocyclic group, each of which may have a substituent; andAr¹⁰¹ and R²⁰¹ may be linked to each other to form a ring.

The wavelength conversion luminescent resin composition and thewavelength conversion member of the present invention can realize a highquantum yield by including a pyrromethene boron complex having aspecific structure.

DESCRIPTION OF THE PREFERRED EMBODIMENTS

Hereinafter, embodiments of the present invention will be described indetail.

In the present specification, the numerical range indicated by using theindication “to” means a range including numerical values describedbefore and after “to” as a minimum value and a maximum value,respectively.

According to the wavelength conversion luminescent resin compositionaccording to the embodiment of the present invention, a wavelengthconversion material with high quantum yield and high luminous efficiencycan be prepared since a compound having a specific structure is used inthe composition. The compound represented by Formula (1) used in thepresent invention can prevent the aggregation of the compound byintroducing an aromatic group having a substituent at the ortho positionto the benzo position, whereby a decrease in quantum yield due toaggregation can be suppressed.

[Wavelength Conversion Luminescent Resin Composition]

The wavelength conversion luminescent resin composition according to theembodiment of the present invention is a wavelength conversionluminescent resin composition containing at least one compoundrepresented by Formula (1) and a resin.

The meaning of each symbol in Formula (1) is as defined in the presentspecification.

<Compound Represented by Formula (1)>

In the present specification, the alkyl group may be any of linear,branched, cyclic, or a combination thereof, and the number of carbonatoms in the linear or branched alkyl group is preferably 1 to 36, morepreferably 1 to 18, still more preferably 1 to 12, and particularlypreferably 1 to 6. Examples of the cyclic alkyl group include acycloalkyl group having 3 to 8 carbon atoms. Specific examples of thealkyl group include a methyl group, an ethyl group, an n-propyl group,an isopropyl group, an n-butyl group, an iso-butyl group, a sec-butylgroup, a t-butyl group, an n-pentyl group, an n-hexyl group, an n-heptylgroup, an n-octyl group, an n-nonyl group, an n-decyl group, ann-undecyl group, an n-dodecyl group, an n-tridecyl group, ann-tetradecyl group, an n-pentadecyl group, an n-hexadecyl group, ann-heptadecyl group, an n-octadecyl group, and a cyclohexyl group.

In the present specification, the aryl group is preferably an aryl grouphaving 6 to 48 carbon atoms, more preferably an aryl group having 6 to24 carbon atoms, and still more preferably an aryl group having 6 to 14carbon atoms, examples of which include a phenyl group, a naphthylgroup, an anthryl group, a pyrenyl group, a phenanthrenyl group, abiphenyl group, and a fluorenyl group.

In the present specification, the heterocyclic group may be preferably a5- to 7-membered substituted or unsubstituted, saturated or unsaturated,aromatic or non-aromatic, monocyclic or fused heterocyclic group. Theheterocyclic group is more preferably a heterocyclic group in which thering-constituting atom is selected from a carbon atom, a nitrogen atom,an oxygen atom, and a sulfur atom and which has at least one hetero atomof a nitrogen atom, an oxygen atom, or a sulfur atom, and still morepreferably a 5- or 6-membered aromatic heterocyclic group having 3 to 30carbon atoms. Examples of the heterocyclic group include a furyl group,a benzofuryl group, a dibenzofuryl group, a thienyl group, abenzothienyl group, a dibenzothienyl group, a pyridyl group, apyrimidinyl group, a quinolyl group, an isoquinolyl group, an acridinylgroup, a phenanthridinyl group, a pteridinyl group, a pyrazinyl group, aquinoxalinyl group, a pyrimidinyl group, a quinazolyl group, apyridazinyl group, a cinnolinyl group, a phthalazinyl group, a triazinylgroup, an oxazolyl group, a benzoxazolyl group, a thiazolyl group, abenzothiazolyl group, an imidazolyl group, a benzimidazolyl group, apyrazolyl group, an indazolyl group, an isoxazolyl group, abenzisoxazolyl group, an isothiazolyl group, a benzisothiazolyl group,an oxadiazolyl group, a thiadiazolyl group, a triazolyl group, atetrazolyl group, a furyl group, a thienyl group, a pyrrolyl group, anindolyl group, an imidazopyridinyl group, and a carbazolyl group.

In the present specification, the silyl group is preferably asubstituted or unsubstituted silyl group having 0 to 30 carbon atoms,examples of which include a trimethylsilyl group, a t-butyldimethylsilylgroup, and a phenyldimethylsilyl group.

In the present specification, the acyl group is preferably a linear orbranched alkanoyl group having 2 to 15 carbon atoms, examples of whichinclude an acetyl group, a propionyl group, a butyryl group, anisobutyryl group, a valeryl group, an isovaleryl group, a pivaloylgroup, a hexanoyl group, a heptanoyl group, and a benzoyl group.

In the present specification, the alkoxy group is preferably an alkoxygroup having 1 to 20 carbon atoms, examples of which include a methoxygroup, an ethoxy group, a propoxy group, an n-butoxy group, a pentyloxygroup, a hexyloxy group, and a heptyloxy group.

In the present specification, the aryloxy group is preferably an aryloxygroup having 6 to 14 carbon atoms, examples of which include a phenoxygroup, a naphthoxy group, and an anthryloxy group.

The alkylthio group is preferably an alkylthio group having 1 to 30carbon atoms, examples of which include a methylthio group, an ethylthiogroup, and an n-hexadecylthio group.

The arylthio group is preferably an arylthio group having 6 to 30 carbonatoms, examples of which include a phenylthio group, ap-chlorophenylthio group, and an m-methoxyphenylthio group.

In the present specification, examples of the halogen atoms include afluorine atom, a chlorine atom, a bromine atom, and an iodine atom.

In the present specification, the aromatic ring may be, for example, anaromatic hydrocarbon ring such as a benzene ring, a naphthalene ring, ananthracene ring, a phenanthrene ring, a pyrene ring, a perylene ring, ora terylene ring; an aromatic heterocyclic ring such as an indene ring,an azulene ring, a pyridine ring, a pyrazine ring, a pyrimidine ring, apyrazole ring, a pyrazolidine ring, a thiazolidine ring, an oxazolidinering, a pyran ring, a chromene ring, a pyrrole ring, a pyrrolidine ring,a benzimidazole ring, an imidazoline ring, an imidazolidine ring, animidazole ring, a triazole ring, a triazine ring, a diazole ring, anindoline ring, a thiophene ring, a thienothiophene ring, a furan ring,an oxazole ring, an oxadiazole ring, a thiazine ring, a thiazole ring,an indole ring, a benzothiazole ring, a benzothiadiazole ring, anaphthothiazole ring, a benzoxazole ring, a naphthoxazole ring, anindolenine ring, a benzindolenine ring, a quinoline ring, or aquinazoline ring; and a fused aromatic ring such as a fluorene ring or acarbazole ring. Aromatic rings having 5 to 16 carbon atoms (an aromaticring and a fused ring containing an aromatic ring) are preferable.

Incidentally, the aromatic ring may have a substituent, and the term“aromatic ring” means both an aromatic ring having a substituent and anaromatic ring having no substituent. The substituent of the aromaticring may be, for example, the substituent described in Substituent groupA which will be described later.

In the present specification, examples of the amino group include anamino group; an alkyl-substituted amino group such as a mono- ordimethylamino group, a mono- or diethylamino group, or a mono- ordi(n-propyl)amino group; an amino group substituted with an aromaticresidue, such as a mono- or diphenylamino group or a mono- ordinaphthylamino group; an amino group substituted with one alkyl groupand one aromatic residue, such as a monoalkylmonophenylamino group; abenzylamino group, an acetylamino group, and a phenylacetylamino group.Here, the aromatic residue means a group obtained by removing onehydrogen atom from an aromatic ring, and the aromatic ring is asdescribed hereinabove.

The alkyl group, aryl group, hydroxy group, alkoxy group, or aryloxygroup represented by Y¹ and Y² may have a substituent, examples of whichinclude the substituents described in Substituent group A shown below.

Substituent group A: a sulfamoyl group, a cyano group, an isocyanogroup, a thiocyanato group, an isothiocyanato group, a nitro group, anitrosyl group, a halogen atom, a hydroxy group, an amino group, amercapto group, an amide group, an alkoxy group, an aryloxy group, analkylthio group, an arylthio group, a carbamoyl group, an acyl group, analdehyde group, a carbonyl group, an aryl group, an alkyl group, analkyl group substituted with a halogen atom, an ethenyl group, anethynyl group, a silyl group, and a trialkylsilyl group (for example, atrimethylsilyl group).

In a case where R³ represents an alkyl group, an aryl group, aheterocyclic group, an ethenyl group, an ethynyl group, or an acylgroup, each group may have a substituent, examples of which include thesubstituents described in Substituent group A.

The aryl group represented by Ar³ and Ar⁴ may have a substituent,examples of which include the substituents described in Substituentgroup A.

In a case where R⁴ to R¹¹ represent an alkyl group, an aryl group, aheterocyclic group, an ethenyl group, an ethynyl group, an acyl group,an alkoxy group, an aryloxy group, an alkylthio group, an arylthiogroup, or an amino group, each group may have a substituent, examples ofwhich include the substituents described in Substituent group A.

The alkyl group, aryl group, heterocyclic group, ethenyl group, ethynylgroup, acyl group, silyl group, alkoxy group, aryloxy group, alkylthiogroup, arylthio group, or amino group represented by R²⁰¹ may have asubstituent, examples of which include the substituents described inSubstituent group A.

Q represents an aromatic ring which may have a substituent, examples ofwhich include the substituents described in Substituent group A.

The alkyl group, aryl group, heterocyclic group, ethenyl group, ethynylgroup, or acyl group represented by R¹⁰¹ may have a substituent,examples of which include the substituents described in Substituentgroup A.

The aryl group or heterocyclic group represented by Ar¹⁰¹ may have asubstituent, examples of which include the substituents described inSubstituent group A.

In Formula (1), Y¹ and Y² each independently represent a halogen atom,an alkyl group, an aryl group, a hydroxy group, an alkoxy group, or anaryloxy group, each of which may have a substituent, and Y¹ and Y² maybe linked to each other to form a ring.

Preferably, Y¹ and Y² each independently represent a halogen atom or analkoxy group, and more preferably each independently represent a halogenatom.

Still more preferably, Y¹ and Y² are fluorine atoms.

In Formula (1), R³ represents a hydrogen atom, an alkyl group, an arylgroup, a heterocyclic group, an ethenyl group, an ethynyl group, or anacyl group, each of which may have a substituent.

R³ is preferably a hydrogen atom, an alkyl group, an aryl group, or aheterocyclic group, and more preferably a hydrogen atom, an alkyl group,or an aryl group, each of which may have a substituent.

Still more preferably, R³ is a hydrogen atom.

In Formula (1), Ar³ and Ar⁴ each independently represent an aryl group,which may have a substituent.

Ar³ and Ar⁴ are preferably each independently a substituent representedby Formula (2).

In Formula (2), R²⁰¹ represents a halogen atom, an alkyl group, an arylgroup, a heterocyclic group, an ethenyl group, an ethynyl group, an acylgroup, a silyl group, an alkoxy group, an aryloxy group, an alkylthiogroup, an arylthio group, or an amino group, each of which may have asubstituent; and Q represents an aromatic ring which may have asubstituent.

R²⁰¹ preferably represents a halogen atom, an alkyl group, an arylgroup, an acyl group, a silyl group, an alkoxy group, an aryloxy group,an alkylthio group, an arylthio group, or an amino group, morepreferably a halogen atom, an alkyl group, an aryl group, an alkoxygroup, or an aryloxy group, still more preferably a halogen atom, analkyl group, an alkoxy group, or an aryl group, and particularlypreferably a halogen atom or an alkyl group.

Ar³ and Ar⁴ are more preferably each independently is a substituentrepresented by Formula (5).

In Formula (5), R²⁰¹ to R²⁰⁵ each represent a hydrogen atom, a halogenatom, an alkyl group, an aryl group, a heterocyclic group, an ethenylgroup, an ethynyl group, an acyl group, a silyl group, an alkoxy group,an aryloxy group, an alkylthio group, an arylthio group, or an aminogroup, and at least one of R²⁰¹ or R²⁰⁵ is a group other than a hydrogenatom; and R²⁰¹ and R²⁰² may be linked to each other to form a ring, R²⁰²and R²⁰³ may be linked to each other to form a ring, R²⁰³ and R²⁰⁴ maybe linked to each other to form a ring, and R²⁰⁴ and R²⁰⁵ may be linkedto each other to form a ring.

R²⁰¹ to R²⁰⁵ preferably each independently represent a hydrogen atom, ahalogen atom, an alkyl group, an aryl group, an acyl group, a silylgroup, an alkoxy group, an aryloxy group, an alkylthio group, anarylthio group, or an amino group, more preferably a hydrogen atom, ahalogen atom, an alkyl group, an aryl group, an alkoxy group, or anaryloxy group, still more preferably a hydrogen atom, a halogen atom, analkyl group, or an aryl group, and particularly preferably a hydrogenatom, a halogen atom, or an alkyl group.

In Formula (1), R⁴ to R¹¹ each independently represent a hydrogen atom,a halogen atom, an alkyl group, an aryl group, a heterocyclic group, anethenyl group, an ethynyl group, an acyl group, an alkoxy group, anaryloxy group, an alkylthio group, an arylthio group, or an amino group,each of which may have a substituent, and at least one of R⁴, . . . , orR¹¹ represents a substituent represented by Formula (2) or Formula (3).

R⁴ to R¹¹ preferably each independently represent a hydrogen atom, ahalogen atom, an alkyl group, an aryl group, an ethenyl group, anethynyl group, an alkoxy group, an aryloxy group, an alkylthio group, anarylthio group, or an amino group, more preferably each independentlyrepresent a hydrogen atom, a halogen atom, an alkyl group, an arylgroup, an alkoxy group, an aryloxy group, or an amino group, still morepreferably each independently represent a hydrogen atom, an alkyl group,an aryl group, an alkoxy group, or an amino group, and particularlypreferably each independently represent a hydrogen atom, an alkyl group,an aryl group, or an alkoxy group.

In Formula (2), R²⁰¹ represents a halogen atom, an alkyl group, an arylgroup, a heterocyclic group, an ethenyl group, an ethynyl group, an acylgroup, a silyl group, an alkoxy group, an aryloxy group, an alkylthiogroup, an arylthio group, or an amino group, each of which may have asubstituent; and Q represents an aromatic ring which may have asubstituent.

R²⁰¹ preferably represents a halogen atom, an alkyl group, an arylgroup, an acyl group, a silyl group, an alkoxy group, an aryloxy group,an alkylthio group, an arylthio group, or an amino group, morepreferably a halogen atom, an alkyl group, an aryl group, an alkoxygroup, or an aryloxy group, still more preferably a halogen atom, analkyl group, an alkoxy group, or an aryl group, and particularlypreferably a halogen atom or an alkyl group.

In Formula (3), R¹⁰¹ represents an alkyl group, an aryl group, aheterocyclic group, an ethenyl group, an ethynyl group, or an acylgroup, each of which may have a substituent; Ar¹⁰¹ represents an arylgroup or a heterocyclic group, each of which may have a substituent; andAr¹⁰¹ and R²⁰¹ may be linked to each other to form a ring.

Preferably, at least one of R⁴, . . . , or R¹¹ is a substituentrepresented by Formula (2).

More preferably, at least one of R⁴, . . . , or R¹¹ represents asubstituent represented by Formula (5).

In Formula (5), R²⁰¹ to R²⁰⁵ each represent a hydrogen atom, a halogenatom, an alkyl group, an aryl group, a heterocyclic group, an ethenylgroup, an ethynyl group, an acyl group, a silyl group, an alkoxy group,an aryloxy group, an alkylthio group, an arylthio group, or an aminogroup, and at least one of R²⁰¹ or R²⁰⁵ is a group other than a hydrogenatom; and R²⁰¹ and R²⁰² may be linked to each other to form a ring, R²⁰²and R²⁰³ may be linked to each other to form a ring, R²⁰³ and R²⁰⁴ maybe linked to each other to form a ring, and R²⁰⁴ and R²⁰⁵ may be linkedto each other to form a ring.

R²⁰¹ to R²⁰⁵ preferably each independently represent a hydrogen atom, ahalogen atom, an alkyl group, an aryl group, an acyl group, a silylgroup, an alkoxy group, an aryloxy group, an alkylthio group, anarylthio group, or an amino group, more preferably a hydrogen atom, ahalogen atom, an alkyl group, an aryl group, an alkoxy group, or anaryloxy group, still more preferably a hydrogen atom, a halogen atom, analkyl group, or an aryl group, and particularly preferably a hydrogenatom, a halogen atom, or an alkyl group.

In the resin composition of the present invention, the compoundrepresented by Formula (1) may be used alone, or a plurality of types ofcompounds represented by Formula (1) may be used in combination.

<Specific Example of Compound Represented by Formula (1)>

Specific examples of the compound represented by Formula (1) aredescribed below. Me represents a methyl group, and Ph represents aphenyl group.

<Method for Producing Compound Represented by Formula (1)>

The compound represented by Formula (1) can be produced, for example, bythe synthesis scheme shown in the Examples which will be describedlater.

As an example, the synthesis of Compound (1) of the Examples is outlinedbelow.

Compound (1-A) can be synthesized according to the method described inBioorganic & Medicinal Chemistry 2004, 12, pp. 2079 to 2098. As Compound(1-B), a commercially available product manufactured by Alfa Aesar, Inc.or the like can be used. Compound (1-C) can be synthesized according tothe method described in Macromolecules 2010, 43, pp. 193 to 200 usingCompound (1-A) and Compound (1-B) as starting materials.

Compound (1-C), 2,4,6-trimethylphenylboronic acid, and cesium fluorideare added to a mixed solution of dimethoxyethane and water, followed bydegassing by repeating evacuation and purging with nitrogen. Palladiumacetate and 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl are addedthereto and the temperature of the reaction system is raised. Compound(1) can be produced by reaction under reflux.

The compound represented by Formula (1) other than Compound (1) can alsobe produced by replacing the compound used in the reaction with acompound having a substituent corresponding to the desired compoundrepresented by Formula (1).

<Luminescent Resin Composition>

The resin used in the luminescent resin composition of the presentinvention may be any of a thermoplastic polymer compound, a heat- orphoto-curable polymer compound, or a mixture thereof. In the presentspecification, the term “polymer compound” means that it also includes amonomer or polymerization precursor of a polymer compound, in a casewhere the polymer compound is a heat- or photo-curable polymer compound.

In addition, the wavelength conversion luminescent resin compositionaccording to the embodiment of the present invention takes a form otherthan particles (non-particle form). Therefore, the resin is not used inthe form of particles in the present invention.

The resin used in the present invention is preferably transparent(transmittance of visible light (wavelength of 300 to 830 nm) is 50% ormore) or translucent. Specific examples of the resin include an acrylicresin, a methacrylic resin, a curable polymer compound having a reactivevinyl group such as vinyl polycinnamate, a polycarbonate, a polyimide, apolyamideimide, a polyesterimide, a polyetherimide, a polyetherketone, apolyether ether ketone, a polyether sulfone, a polysulfone, apolyparaxylene, a polyester, a polyvinyl acetal, a polyvinyl chloride, apolyvinyl acetate, a polyamide, a polystyrene, a polyurethane, apolyvinyl alcohol, a cellulose acylate, a fluorinated resin, a siliconeresin, an epoxy silicone resin, a phenol resin, an alkyd resin, an epoxyresin, a malcic acid resin, a melamine resin, a urea resin, an aromaticsulfonamide, a benzoguanamine resin, a silicone-based elastomer, and acyclic olefin copolymer. These resins may be used alone or incombination of two or more thereof. Those having a molecular weight ofabout 1,000 to 100,000 as a weight-average molecular weight can usuallybe used, but resin compounds having a molecular weight outside thisrange can also be used.

In the luminescent resin composition of the present invention, theamount of the compound represented by Formula (1) with respect to theresin is not particularly limited but is usually preferably 0.01% to 80%by mass, more preferably 0.01% to 60% by mass, and most preferably 0.01%to 30% by mass with respect to the total mass of the resin.

In the composition of the present invention, at least one compoundrepresented by Formula (1) is used, but two or more compoundsrepresented by Formula (1) may be used. In a case where two or morecompounds represented by Formula (1) are used, it is preferred that thetotal amount thereof falls within the above range.

The luminescent resin composition of the present invention can alsocontain, for example, a coloring agent for tone correction, aprocessing/oxidation and heat stabilizer (antioxidant, phosphorus-basedprocessing stabilizer, or the like), a light resistance stabilizer (anultraviolet absorber, or the like), and a silane coupling agent, inaddition to the compound represented by Formula (1) and the resin.

Specific examples of the coloring agent for tone correction include aperylene-based pigment, an anthraquinone-based pigment, a lake-basedpigment, an azo-based pigment, a quinacridone-based pigment, ananthracene-based pigment, an isoindoline-based pigment, anisoindolinone-based pigment, a phthalocyanine-based pigment, atriphenylmethane-based basic dye, an indanthrone-based pigment, anindophenol-based pigment, a cyanine-based pigment, a dioxazine-basedpigment, a coumarin-based dye, and a mixture of two or more thereof.

Specific examples of processing/oxidation and heat stabilizer includephosphite esters such as tributyl phosphite,tris(2-ethylhexyl)phosphite, tridecyl phosphite, tristearyl phosphite,triphenyl phosphite, tricresyl phosphite, tris(nonylphenyl)phosphite,tris(2,4-di-tert-butylphenyl)phosphite, decyl-diphenyl phosphite,phenyl-di-2-ethylhexyl phosphite, phenyl-didecyl phosphite,tricyclohexyl phosphite, distearyl-pentaerythrityl-diphosphite,tris(mixed mono-, di-phenyl)phosphite,dinonylphenyl-bis(nonylphenyl)phosphite, andoctyl-[2,2′-di(4,6-di-tert-butylphenyl) methylene]phosphate;

phosphines such as triethylphosphine, triisopropylphosphine,tri-n-butylphosphine, tricyclohexylphosphine, allyldiphenylphosphine,triphenylphosphine, diphenylphosphine,tris(2,4-dimethylphenyl)phosphine, tris(2,4,6-trimethylphenyl)phosphine,tris(o-tolyl)phosphine, tris(o-anisyl)phosphine, diphenylbutylphosphine,diphenyloctadecylphosphine, tris(p-nonylphenyl)phosphine,tris(naphthyl)phosphine, diphenyl-(hydroxymethyl)phosphine,diphenylbenzylphosphine, diphenyl-(p-hydroxyphenyl)phosphine,diphenyl-(2,5-dihydroxyphenyl)phosphine, andphenylnaphthylbenzylphosphine; phosphonites such astriphenylphosphonite, dinonylphenylphosphonite,diisooctylphenylphosphonite,phenyl(2,4,6-trimethylphenyl)phenylphosphonite, andtetrakis(2,4-di-tert-butylphenyl)-4′,4″-biphenylene diphosphonite; andphenolic antioxidants such as 2,6-di-tert-butyl-p-cresol,2,6-di-tert-butyl-p-ethylphenol,2,2′-methylenebis(6-tert-butyl-p-cresol),4,4′-methylenebis(6-tert-butyl-o-cresol),4,4′-methylenebis(6-tert-butyl-m-cresol),tetrakis-[methylene-3-(3′,5′-di-tert-butyl-4′-hydroxyphenyl)propionate]methane,4,4′-thiobis(6-tert-butyl-m-cresol),stearyl-β-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate,1,3,5-trimethyl-2,4,6-tris(3,5-di-tert-butyl-4-hydroxybenzyl)benzene,octadecyl 3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate, and3,5-di-tert-butyl-4-hydroxybenzylphosphonate-diethyl ester. Theseprocessing, oxidation, and heat stabilizers may be used alone or incombination of two or more thereof.

Examples of the light resistance stabilizer include benzotriazoles suchas 2-(5-methyl-2-hydroxyphenyl)benzotriazole,2-[2-hydroxy-3,5-bis(α,α-dimethylbenzyl)phenyl]-2H-benzotriazole, and3′,3′-bis[2-(5′-octyl-2′-hydroxyphenyl)benzotriazodyl]methane. Theselight resistance stabilizers may be used alone or in combination of twoor more thereof.

The silane coupling agent is preferably a compound having an epoxy groupor an amino group, specific examples of which includeβ-(3,4-epoxycyclohexyl)ethyltrimethoxysilane,γ-glycidoxypropyltrimethoxysilane,γ-glycidoxypropylmethyldiethoxysilane,N-β-aminoethyl-γ-aminopropyltrimethoxysilane,n-β-aminoethyl-γ-aminopropylmethyldimethoxysilane,γ-aminopropyltriethoxysilane, andN-phenyl-γ-aminopropyltrimethoxysilane.

The coloring agent for tone correction, the processing/oxidation andheat stabilizer, the light resistance stabilizer, and the silanecoupling agent are preferably added in an amount exhibiting tonecorrection effects and stabilizing effects, and are preferably used inan amount of usually about 0.1 ppm to 10% by mass with respect to themass of the resin.

Additives such as an organic acid, a matting agent, a radical scavenger,a deterioration inhibitor, a filler (for example, silica, glass fiber,or glass beads), a plasticizer, a lubricant, a flame retardant (forexample, an organohalogen-based compound), a flame retardant aid, anantistatic agent, a chargeability imparting agent, an impact modifier, adiscoloration preventing agent, a releasing agent (for example, a higherfatty acid ester of a monohydric or polyhydric alcohol), a flowabilityimprover, and a reactive or non-reactive diluent can be blendedappropriately in the luminescent resin composition of the presentinvention.

[Method for Producing Wavelength Conversion Luminescent ResinComposition]

The method for producing a wavelength conversion luminescent resincomposition according to the embodiment of the present invention is notparticularly limited and examples thereof include the following methods.

(Method A) A Method Including a Step of Drying a Solution Containing atLeast One Compound Represented by Formula (1) and a Resin in a Solvent:

For example, the organic solvent can be removed by dissolving orsuspending the compound represented by Formula (1) in an organic solventsolution of the resin, followed by heating and drying.

(Method B) A Method Including a Step of Curing a Composition Containingat Least One Compound Represented by Formula (1) and a Monomer and/or aPolymerization Precursor:

After dispersing the compound represented by Formula (1) in a monomer orpolymerization precursor of a heat- or photo-curable polymer, themonomer or polymerization precursor can be polymerized. Alternatively,after dissolving or suspending the compound represented by Formula (1)in a solution of the monomer or polymerization precursor, the organicsolvent may be removed to polymerize the monomer or polymerizationprecursor.

(Method C) A Method Including a Step of Melting a Composition Containingat Least One Compound Represented by Formula (1) and a Resin:

For example, melting can be made after dispersing the compoundrepresented by Formula (1) in a resin.

As a method of dispersing the compound represented by Formula (1) in theresin, it is possible to use melt blending, mixing with a powder of apolymer compound, or the like. In a case where melt blending is carriedout, a common device used for melt blending rubber or plastics, forexample, a heat roll, a tumbler mixer, a V-blender, a Nauta mixer, aHenschel mixer, a ribbon blender, a super mixer, a Banbury mixer, aBrabender, or an extruder can be used. The melting temperature ispreferably set at a temperature at which the resin is meltable and whichis equal to or lower than the temperature at which the resin begins tothermally decompose, and the temperature is usually 150° C. to 450° C.and preferably 180° C. to 400° C. In a case where the compoundrepresented by Formula (1) is dispersed in the monomer or polymerizationprecursor, a method of dispersing the compound represented by Formula(1) in a liquid of the monomer using, for example, a paint shaker, amixer, or a homogenizer can be used in a case where the monomer orpolymerization precursor is a liquid, and a method of dispersing thecompound represented by Formula (1) in a powder of the monomer using,for example, a ball mill or a sand mill can be used in a case where themonomer is a solid.

As the organic solvent used for dispersing or dissolving the compoundrepresented by Formula (1) using an organic solvent as a medium, forexample, hydrocarbons such as hexane, octane, decane, toluene, xylene,ethylbenzene, and 1-methylnaphthalene; ketone-based solvents such asacetone, methyl ethyl ketone, methyl isobutyl ketone, and cyclohexanone;halogenated hydrocarbon solvents such as dichloromethane, chloroform,tetrachloroethane, dichloroethane, trichloroethane, tetrachloroethane,chlorobenzene, dichlorobenzene, and chlorotoluene; ester-based solventssuch as ethyl acetate, butyl acetate, and amyl acetate; alcohol-basedsolvents such as methanol, ethanol, propanol, butanol, pentanol,hexanol, cyclohexanol, methyl cellosolve, ethyl cellosolve, ethyleneglycol, and diethylene glycol; ether-based solvents such as dibutylether, tetrahydrofuran, dioxane, and anisole; polar solvents such asN,N-dimethylformamide, N,N-dimethylacetamide, l-methyl-2-pyrrolidone,1,3-dimethylimidazolidinone, and dimethyl sulfoxide; and water can beused. These organic solvents may be used alone or in combination of twoor more thereof. As a method of removing the organic solvent, a methodin which the mixed organic solvent solution is heated to a temperatureequal to or higher than the boiling point of the organic solvent andequal to or lower than the decomposition temperature of the polymercompound or monomer and the pyrromethene boron complex compound toevaporate and remove the organic solvent may be used, or alternatively,a method of evaporating and removing the organic solvent under reducedpressure (equal to or lower than atmospheric pressure) pressure may beused.

In a case where the resin is a thermoplastic polymer compound, themethod of molding the luminescent resin composition of the presentinvention can be carried out by a molding method such as injectionmolding, compression molding, transfer molding, or extrusion molding. Ina case where the resin is a heat- or photo-curable polymer compound, thepolymerization method may be carried out by common thermopolymerizationor photopolymerization. In a case of thermopolymerization, it canusually be carried out by adding a catalyst to the luminescent resincomposition of the present invention as needed, followed by heating. Theheating temperature is usually in the range from room temperature to theglass transition temperature or melting point of the target polymercompound or higher, but it may be gradually raised from around roomtemperature in accordance with the progress of polymerization. Examplesof the catalyst include a radical polymerization catalyst, an anionicpolymerization catalyst, a cationic polymerization catalyst, and ahydrosilylation catalyst. Examples of the radical polymerizationcatalyst include azobisisobutyronitrile, benzoyl peroxide,di-3-methoxybutyl peroxydicarbonate, diisopropyl peroxycarbonate,α-cumyl peroxyneodecanoate, tert-butylperoxy-2-ethylhexanoate, dicumylperoxide, 1,1-di-tert-butylperoxy-3,3,5-trimethylcyclohexane, andtert-butylcumyl peroxide.

Examples of the anionic polymerization catalyst includetetrabutylammonium chloride, tetrabutylammonium hydroxide,triethylamine, tributylamine, pyridine, N-methylpyrrolidone, piperidine,triphenylphosphine, tributylphosphine, triethanolamine,methyldiethanolamine, triisopropanolamine,4,4′-dimethylaminobenzophenone, 2-dimethylaminoethylbenzoic acid, ethyldimethylaminobenzoate, isoamyl dimethylaminobenzoate, (n-butoxy)ethyldimethylaminobenzoate, isoamyl 2-dimethylaminoethylbenzoate, and2-ethylhexyl 2-dimethylaminoethylbenzoate.

Examples of the cationic polymerization catalyst include sulfuric acid,hydrochloric acid, p-toluenesulfonic acid, methanesulfonic acid,phosphoric acid, acetic acid, propionic acid, dibutyltin dioxide,dimethyltin dichloride, dibutyltin dichloride, dibutyltin dilaurate,tetrabutyltin, boron trifluoride, tetraethoxy titanium, and titaniumoxide. The addition amount of these polymerization catalysts greatlyvaries depending on the type of the monomer and/or the polymerizationprecursor and the composition containing them and therefore is notparticularly limited, but it is usually in the range of 0.0001% to 10%by mass with respect to the mass of the monomer and/or thepolymerization precursor.

The hydrosilylation catalyst may be, for example, platinum.

In a case of photopolymerization, polymerization is carried out byadding a photopolymerization initiator to the luminescent resincomposition, if necessary, followed by irradiation with light. Inaddition, the radical polymerization catalyst, the anionicpolymerization catalyst, the cationic polymerization catalyst, and thelike may be used in combination. Examples of the photopolymerizationinitiator include a photo radical generator, a photo anion generator,and a photo cation generator, among which a photo radical generator anda photo cation generator are preferable. Examples of the photo radicalgenerator include 4-phenoxydichloroacetophenone,4-tert-butyldichloroacetophenone, diethoxyacetophenone,2-hydroxy-2-methyl-1-phenylpropan-1-one,1-(4′-isopropylphenyl)-2-hydroxy-2-methylpropan-1-one,1-(4′-dodecylphenyl)-2-hydroxy-2-methylpropan-1-one, 1-hydroxycyclohexylphenyl ketone,2-methyl-1-[4′-(methylthio)phenyl]-2-morpholinopropan-1-one, benzoin,benzoin methyl ether, benzoin ethyl ether, benzoin isobutyl ether,benzoin dimethyl ketal, benzophenone, benzoyl benzoic acid, methylbenzoylbenzoate, 4-phenylbenzophenone, hydroxybenzophenone, allylatedbenzophenone, 4-benzoyl-4′-methyldiphenylsulfide,3,3′-dimethyl-4-methoxybenzophenone, thioxanthone, 2-chlorothioxanthone,2-methylthioxanthone, isopropylthioxanthone, 2,4-dichlorothioxanthone,2,4-dimethylthioxanthone, 2,4-diethylthioxanthone,2,4-diisopropylthioxanthone,2,4,6-trimethylbenzoyldiphenylphosphineoxide, methylphenylglyoxylate,dibenzyl, 9,10-phenanthrenequinone, camphorquinone, dibenzosuberone,2-ethylanthraquinone, 4′,4″-diethylisophthaloquinone, and3,3′,4,4′-tetra(tert-butylperoxycarbonyl)benzophenone. The additionamount thereof greatly varies depending on the type of the monomerand/or the polymerization precursor and the composition containing themand therefore is not particularly limited, but it is usually in therange of 0.0001% to 10% by mass with respect to the mass of the monomerand/or the polymerization precursor.

Examples of the photo cation generator include an aromatic diazoniumsalt, an aromatic sulfonium salt, an aromatic iodonium salt, an oniumsalt of Brønsted acid, and an iron aromatic compound salt, among whichan aromatic sulfonium salt, an aromatic iodonium salt, and an ironaromatic compound salt of Brønsted acid are preferably used. Examples ofthe aromatic sulfonium salt include a terphenylsulfoniumtetrafluoroborate salt, a triphenylsulfonium hexafluorophosphonium salt,and a triphenylsulfonium hexafluoroantimonium salt.

CYRACURE UVI-6974 (manufactured by UCC), CYRACURE UVI-6990 (manufacturedby UCC), OPTOMER SPI50 (manufactured by Asahi Denka Kogyo K.K.), OPTOMERSP170 (manufactured by Asahi Denka Kogyo K.K.), and the like, which areall trade names and are commercially available as modified versions ofaromatic sulfonium salts capable of generating free radicals, can alsobe mentioned. As the iron aromatic compound salt of Brønsted acid, thetrade name: CG 24-061 (manufactured by Ciba-Geigy AG) can be mentioned.The addition amount thereof greatly varies depending on the type of themonomer and/or the polymerization precursor and the compositioncontaining them and therefore is not particularly limited, but it isusually in the range of 0.0001% to 10% by mass with respect to the massof the monomer and/or the polymerization precursor. Ultraviolet light orvisible light of about 100 to 800 nm is preferably used as the radiatedlight. In a case where ultraviolet light of 400 nm or less is used, alight source such as a low-pressure mercury lamp, a high-pressuremercury lamp, an extra-high pressure mercury lamp, a metal halide lamp,a pulse xenon lamp, or an electrodeless discharge lamp is preferablyused.

[Wavelength Conversion Member]

The wavelength conversion member according to the embodiment of thepresent invention can be obtained by molding the luminescent resincomposition for a wavelength conversion member according to theembodiment of the present invention. The molding method may be carriedout by a method of molding in a hot melt state such as injectionmolding, or a method in which a solution is prepared with an organicsolvent capable of dissolving a resin and then a film is formed by aspin coating method, a roll coating method, a bar coating method, aLangmuir-Blodgett method, a casting method, a dipping method, a screenprinting method, a BUBBLE JET (registered trademark) method, or an inkjet method. In a case where the resin contained in the luminescent resincomposition of the present invention is a heat- or photo-curable polymercompound, the molding method can be carried out by filling a suitablemold with a composition obtained by mixing the monomer and/orpolymerization precursor of the polymer compound and the pyrrometheneboron complex compound, followed by polymerization with light or heat.The shape of the wavelength conversion member is not particularlylimited, and may be various shapes such as a film shape, a plate shape(for example, a sheet shape, a filter shape, or a disc shape), a lensshape, a fiber shape, and an optical waveguide shape.

In a case where the wavelength conversion member according to theembodiment of the present invention is used in the form of a film, asubstrate such as a glass substrate or a polymer substrate may be usedas required. Examples of such substrates include glass substrates suchas soda-lime glass, barium/strontium-containing glass, lead glass,aluminosilicate glass, borosilicate glass, barium/borosilicate glass,and quartz; and polymer substrates such as polycarbonate, acrylic resin,polyethylene terephthalate, polyether sulfide, and polysulfone. In acase of forming a film, it is possible to form a film using variousmethods such as a casting method, a spin coating method, a coatingmethod, a vapor deposition method, an electric field method, a printingmethod, and a casting method.

The wavelength conversion member according to the embodiment of thepresent invention exhibits a high quantum yield by including thecompound represented by Formula (1).

The quantum yield is a ratio of the number of photons emitted asfluorescence to the number of photons absorbed by the luminescentparticles.

The quantum yield of the wavelength conversion member according to theembodiment of the present invention is preferably 0.4 or more, morepreferably 0.5 or more, still more preferably 0.6 or more, even stillmore preferably 0.7 or more, and particularly preferably 0.75 or more.The upper limit of the quantum yield is not particularly limited, butgenerally it is 1.0 or less.

The quantum yield of the luminescent particles of the present inventioncan be measured using a commercially available quantum yield measuringapparatus, for example, an absolute PL quantum yield spectrometerC9920-02 (manufactured by Hamamatsu Photonics K.K.). PL stands forphotoluminescence.

[Application of Present Invention]

The wavelength conversion luminescent resin composition according to theembodiment of the present invention and the wavelength conversion memberaccording to the embodiment of the present invention can be used, forexample, in a light-emitting element. The light-emitting element can beconstituted of a light source and a wavelength conversion member.

The light source is not particularly limited, and examples thereofinclude an incandescent bulb, a metal halide lamp, a high intensitydischarge lamp (HID) lamp), a xenon lamp, a sodium lamp, a mercury lamp,a fluorescent lamp, a cold cathode fluorescent lamp, a cathodeluminescence, a low-speed electron-ray tube, light emitting diode [forexample, GaP (red, green), GaP_(x)As_(1-x) (red, orange, yellow: 0<x<1),Al_(x)Ga_(1-x)As (red: 0<x<1), GaAs (red), SiC (blue), GaN (blue), ZnS,ZnSe], electroluminescence (for example, inorganic EL using a ZnS matrixand a luminescent center, or organic EL), a laser (for example, a gaslaser such as a He—Ne laser, a CO₂ laser, an Ar, Kr, He—Cd laser, anexcimer laser, or a nitrogen laser; a solid laser such as a ruby laser,a YAG laser, or a glass laser; a coloring agent laser, or asemiconductor laser), and sunlight.

A preferred light source is a light emitting diode, electroluminescence,or a semiconductor laser.

The light emitting diode is preferably a semiconductor light-emittingelement having a light emitting layer capable of emitting light having aluminescence wavelength that can excite a fluorescent substance. Avariety of semiconductors such as ZnSe and GaN can be cited as such asemiconductor light-emitting element, but a nitride semiconductor(In_(x)Al_(y)Ga_(1-x-y), 0≤X, 0≤Y, X+Y≤1) capable of emitting lighthaving a short wavelength that can efficiently excite a fluorescentsubstance is preferable. A homo structure, a heterostructure, or adouble heterostructure having a metal-insulator-silicon (MIS) junction,a PIN junction, a pn junction, or the like can be mentioned as asemiconductor structure. A variety of luminescence wavelengths can beselected depending on the material of the semiconductor layer and themixed crystal degree thereof. In addition, the semiconductorlight-emitting element can also be configured to have a single quantumwell structure or a multiple quantum well structure in which asemiconductor active layer is formed in a thin film in which quantumeffects occur.

In a case of emitting light of a white type in a light-emitting element,the luminescence wavelength of the light source is preferably 200 nm ormore and 550 nm or less in consideration of the complementary colorrelationship with the luminescence wavelength from the fluorescentsubstance and deterioration of the transparent polymer compound; and inorder to further improve the excitation of light source and fluorescentsubstance, and the luminous efficiency, respectively, the luminescencewavelength of the light source is more preferably 300 nm or more and 500nm or less. A light emitting diode used as a light source for alight-emitting element is usually placed on a substrate having apatterned metal such as copper foil. Here, an insulating organiccompound or inorganic compound can be mentioned as the substratematerial, and a variety of polymer materials (for example, an epoxyresin and an acrylic resin), inorganic materials (for example, glass andceramics), and the like can be used. In addition, the shape of thesubstrate is not particularly limited, and a variety of shapes such as aplate shape (for example, a sheet shape, a filter shape, or a discshape), a cup shape, and a perforated plate shape can be selected.

As a semiconductor laser that can be used as a light source for alight-emitting element, it is represented by a mechanism in which asemiconductor is pn-junctioned, a forward bias is applied thereto,minority carriers at a high energy level are injected, electrons flowinginto a p-type region are recombined with holes and holes flowing into ann-type region are recombined with electrons, electrons are caused totransition from a high energy level to a low energy level, and photonscorresponding to the energy difference are emitted. As a material of thesemiconductor laser, a group IV element such as germanium or silicon, adirect transition type group III-V or group II-VI compound withoutlattice vibration such as GaAs or InP, and the like can be given. Inaddition, these materials may be multi-element systems such as ternary,quaternary, and quinary systems as well as binary systems. In addition,the laminated structure may be a double heterostructure provided with acladding layer, or may have a structure including a lower cladding, anactive layer, and an upper cladding. Further, the laminated structuremay be one to which a multiple quantum well structure is applied. Thestripe structure for improving the luminous efficiency may be a gainwaveguide type or a refractive index distribution waveguide type.Examples of the gain waveguide type include a sandwich type, a planarstripe type, a groove diffusion type, a proton irradiation type, an ISPtype, a depletion layer control type, and a mesa stripe type. Examplesof the refractive index distribution waveguide type include a CSP type,a PCW type, a TS type, a VSIS type, a TRS type, a groove forming type, aBH type, a DC-PBH type, a V groove type, a U groove type, a mesa type, aTJS type, a DDS type, and a shape distribution type. In addition, theresonator structure may be a distributed feedback (DFB) type or a Braggreflector (DBR) type.

In a case of converting a wavelength of light of a light source using alight source such as a light emitting diode or a semiconductor laser andthe wavelength conversion member according to the embodiment of thepresent invention, if desired, a color filter may be provided to adjustthe color purity. Examples of the color filter include a singlesubstance such as a perylene-based pigment, a lake-based pigment, anazo-based pigment, a quinacridone-based pigment, an anthraquinone-basedpigment, an anthracene-based pigment, an isoindoline-based pigment, anisoindolinone-based pigment, a phthalocyanine-based pigment, atriphenylmethane-based basic dye, an indanthrone-based pigment, anindophenol-based pigment, a cyanine-based pigment, or a dioxazine-basedpigment, a coloring agent only including a mixture of two or morethereof, and one in a solid state where a coloring agent is dissolved ordispersed in a binder resin.

As a configuration of the light-emitting element, the following examplescan be given without being particularly limited thereto.

Light source/wavelength conversion member

Light source/translucent substrate/wavelength conversion member

Light source/wavelength conversion member/translucent substrate

Light source/translucent substrate/wavelength conversionmember/translucent substrate

Light source/wavelength conversion member/color filter

Light source/translucent substrate/wavelength conversion member/colorfilter

Light source/wavelength conversion member/translucent substrate/colorfilter

Light source/translucent substrate/wavelength conversionmember/translucent substrate/color filter

Light source/translucent substrate/wavelength conversion member/colorfilter/translucent substrate

Light source/wavelength conversion member/color filter/translucentsubstrate

The translucent substrate refers to a substrate that can transmitvisible light by 50% or more and specific examples thereof include glasssubstrates (for example, soda-lime glass, barium/strontium-containingglass, lead glass, aluminosilicate glass, borosilicate glass,barium/borosilicate glass, and quartz) and polymer substrates (forexample, polycarbonate, acrylic resin, polyethylene terephthalate,polyether sulfide, and polysulfone). In addition, the shape of thetranslucent substrate is not particularly limited, and may be a plateshape or a lens shape. In a case of preparing a light-emitting elementhaving the above-described structure, the respective constituentelements may be sequentially laminated or may be laminated. In addition,in a case of preparing a light-emitting element, the order thereof isnot particularly limited.

The application of the light-emitting element is not particularlylimited, and the light-emitting element can be used for various purposessuch as for indication, display, traffic signal, traffic display, liquidcrystal backlight, liquid crystal front light, field sequential liquidcrystal display, general lighting equipment, local lighting, andinterior lighting.

Hereinafter, the present invention will be described more specificallywith reference to Examples of the present invention. The materials, theused amount, the ratio, the contents of a treatment, the procedures of atreatment, and the like described in Examples below can be suitablymodified without departing from the spirit of the present invention.Accordingly, the scope of the present invention should not belimitatively interpreted by the specific examples described below.

EXAMPLES

The terms have the following meanings.

MS: mass spectrometry

ESI: electrospray ionization

Me: methyl

Et: ethyl

Bu: n-butyl

PMMA: polymethyl methacrylate

Si resin: silicone resin

PVC: polyvinyl chloride

TPU: thermoplastic polyurethane

PC: polycarbonate

TAC: triacetyl acetate

<Structure of Compounds of Examples and Comparative Examples>

Synthetic Example

Synthesis of Compound (1)

Compound (1) was synthesized according to the above scheme. Compound(1-A) was synthesized according to the method described in Bioorganic &Medicinal Chemistry 2004, 12, pp. 2079 to 2098. As Compound (1-B), acommercially available product manufactured by Alfa Aesar, Inc. wasused. Compound (1-C) was synthesized according to the method describedin Macromolecules 2010, 43, pp. 193 to 200 using Compound (1-A) andCompound (1-B) as starting materials.

Compound (1) was synthesized as follows using Compound (1-C) synthesizedabove.

Compound (1-C) (600 mg, 0.75 mmol), 2,4,6-trimethylphenylboronic acid(494 mg, 3.01 mmol), and cesium fluoride (1.14 g, 7.50 mmol) were addedto a mixed solution of dimethoxyethane (abbreviated as DME, 30 mL) andwater (3 mL), followed by degassing by repeating evacuation and purgingwith nitrogen. Palladium acetate (abbreviated as Pd(OAc)₂, 34 mg, 0.15mmol) and 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (Sphos, 123mg, 0.30 mmol) were added thereto and the temperature of the reactionsystem is raised. This was followed by reaction for 12 hours underreflux, allowing to cool, adding water, and then extraction. The organiclayer was washed with saturated saline, dried over magnesium sulfate,filtered, and concentrated to obtain a crude product. The obtained crudeproduct was purified with a silica gel column (50 vol %chloroform/hexane) to obtain Compound (1) (396 mg, yield: 67%). Thecompound was identified by ESI-MS. ESI-MS: [M+H]⁺=781

Synthesis of Compound (2)

27.4 g of hydrazine monohydrate (manufactured by Wako Pure ChemicalIndustries, Ltd.) and 100 mL of ethanol were added to a 300 mLthree-neck flask. With stirring in an (ice-methanol) bath, a solution of25 g of 2,4,6-trimethylbenzoyl chloride (manufactured by Wako PureChemical Industries, Ltd.) dissolved in 100 mL of methylene chloride wasadded dropwise thereto over 1.5 hours while maintaining the internaltemperature at 5° C. or lower. The resulting reaction solution wasstirred at room temperature for 2.5 hours. A part of the solvent wasdistilled off under reduced pressure, and the resulting crystals werecollected by filtration and dried under reduced pressure (60° C.) toobtain 13.0 g of Compound (2-B).

Compound (2) was synthesized in the same manner as in the synthesis ofCompound (1), except that Compound (1-B) was replaced by Compound (2-B)and 2,4,6-trimethylphenylboronic acid was replaced by1-naphthaleneboronic acid. The compound was identified by ESI-MS.ESI-MS: [M+H]=781

Synthesis of Compound (3)

Compound (3) was synthesized in the same manner as in the synthesis ofCompound (1), except that Compound (1-B) was replaced by Compound (2-B).The compound was identified by ESI-MS. ESI-MS: [M+H]⁺=765

Synthesis of Compound (4)

Compound (4) was synthesized in the same manner as in the synthesis ofCompound (1), except that Compound (1-B) was replaced byp-methoxybenzohydrazine. The compound was identified by ESI-MS. ESI-MS:[M+H]⁺=741

Synthesis of Compound (5)

Compound (5) was synthesized in the same manner as in the synthesis ofCompound (1), except that Compound (1-B) was replaced byp-methoxybenzohydrazine and 2,4,6-trimethylphenylboronic acid wasreplaced by 2,4-dimethoxyphenylboronic acid. The compound was identifiedby ESI-MS. ESI-MS: [M+H]⁺=777

Synthesis of Compound (6)

Compound (6-B) was synthesized by replacing 2,4,6-trimethylbenzoylchloride with 2-methoxybenzoyl chloride in the synthesis of Compound(2-B).

Compound (6) was synthesized in the same manner as in the synthesis ofCompound (1), except that Compound (1-B) was replaced by Compound (6-B),and 2,4,6-trimethylphenylboronic acid was replaced by2,4-dibutoxyphenylboronic acid. The compound was identified by ESI-MS.ESI-MS: [M+H]⁺=945

Synthesis of Compound (7)

Compound (7-B) was synthesized by replacing 2,4,6-trimethylbenzoylchloride with tetrafluorobenzoyl chloride in the synthesis of Compound(2-B).

Compound (7) was synthesized in the same manner as in the synthesis ofCompound (1), except that Compound (1-B) was replaced by Compound (7-B).The compound was identified by ESI-MS. ESI-MS: [M+H]⁺=825

(Synthesis of Comparative Compound 1)

Comparative Compound (1) was synthesized in the same manner as in thesynthesis of Compound (1), except that Compound (1-A) was replaced by2-hydroxyacetophenone. The compound was identified by ESI-MS. ESI-MS:[M+H]⁺=545

(Synthesis of Comparative Compound 2)

Comparative Compound (2) was synthesized in the same manner as in thesynthesis of Compound (1), except that Compound (1-B) was replaced bybenzoylhydrazine and 2,4,6-trimethylphenylboronic acid was replaced byphenylboronic acid. The compound was identified by ESI-MS. ESI-MS:[M+H]⁺=597

Example 3

1 g of polymethyl methacrylate (manufactured by Sigma-Aldrich Co. LLC.)was dissolved in 10 mL of toluene, then 10 mg of Compound (3) was addedto prepare a coloring agent resin solution which was then spin-coated ona glass plate at 2000 rpm and dried on a hot plate at 50° C. to preparea wavelength conversion luminescent resin composition (wavelengthconversion member) (see paragraph [0081] of JP2011-241160A).

Example 4

1 g of liquid A and 1 g of liquid B of a silicone resin (KER-2500,two-component addition-cure silicone resin, manufactured by Shin-EtsuChemical Co., Ltd.) were mixed and 20 mg of Compound (3) was addedthereto, followed by mixing at 2000 rpm and defoaming at 2200 rpm with aplanetary mixer (manufactured by Thinky Corporation, AWATORI RENTARO).The resulting coloring agent mixed liquid was coated on a glass plateand cured by heating on a hot plate at 60° C. for 2 hours and at 150° C.for 4 hours to prepare a wavelength conversion luminescent resincomposition (wavelength conversion member).

Example 5

A wavelength conversion luminescent resin composition (wavelengthconversion member) was prepared in the same manner as in Example 3,except that polymethyl methacrylate was replaced by polyvinyl chloride(manufactured by Sigma-Aldrich Co. LLC.).

Example 6

10 g of thermoplastic urethane (C80A, manufactured by BASF Corporation)and 100 mg of Compound (3) were added to a Laboplast Mill andmelt-kneaded at 200° C. for 10 minutes. Thereafter, the kneaded resinwas sandwiched between iron plates at 200° C., heated for 5 minutes, andpressed at 5 to 10 mPa while cooling (see paragraph [0213] ofWO2015/056779A). The wavelength conversion luminescent resin composition(wavelength conversion member) was prepared as described above.

Example 7

A wavelength conversion luminescent resin composition (wavelengthconversion member) was prepared in the same manner as in Example 3,except that polymethyl methacrylate was replaced by polycarbonate(manufactured by Kanto Chemical Co., Ltd.).

Example 8

A wavelength conversion luminescent resin composition (wavelengthconversion member) was prepared in the same manner as in Example 3,except that polymethyl methacrylate was replaced by triacetyl cellulose(manufactured by Wako Pure Chemical Industries, Ltd.), and toluene wasreplaced by methylene chloride.

Examples 1, 2, and 9 to 20 and Comparative Examples 1 to 3

In Examples 1, 2, and 9 to 15 and Comparative Example 1, wavelengthconversion luminescent resin compositions (wavelength conversionmembers) were prepared in the same manner as in Example 3, except thatthe compound used and the addition amount thereof were changed as shownin the following table.

<Evaluation Method of Wavelength Conversion Member>

The prepared wavelength conversion luminescent resin composition(wavelength conversion member) was cut into 15 mm×15 mm and the quantumyield thereof was measured using an absolute PL quantum yieldspectrometer C9920-02 (manufactured by Hamamatsu Photonics K.K.). Theexcitation wavelength was measured using a wavelength shorter than themaximum absorption wavelength of each compound by 50 nm. Evaluationstandards for quantum yield are shown below.

S: 0.75 or more

A: 0.7 or more and less than 0.75

B: 0.6 or more and less than 0.7

C: 0.5 or more and less than 0.6

D: 0.4 or more and less than 0.5

E: less than 0.4

TABLE 1 Addition amount Quantum Compound (% by mass) Resin yield Example1 Compound (1) 1 PMMA B Example 2 Compound (2) 1 PMMA C Example 3Compound (3) 1 PMMA A Example 4 Compound (3) 1 Si resin A Example 5Compound (3) 1 PVC A Example 6 Compound (3) 1 PS A Example 7 Compound(3) 1 PC A Example 8 Compound (3) 1 TAC A Example 9 Compound (3) 0.1PMMA A Example 10 Compound (3) 0.01 PMMA A Example 11 Compound (3) 20PMMA B Example 12 Compound (4) 1 PMMA D Example 13 Compound (5) 1 PMMA DExample 14 Compound (6) 1 PMMA C Example 15 Compound (7) 1 PMMA AComparative Comparative 1 PMMA E Example 1 Compound (1) ComparativeComparative 1 PMMA E Example 2 Compound (2) * Amount added is % by masswith respect to the resin

It was demonstrated that the wavelength conversion luminescent resincompositions (wavelength conversion members) according to the embodimentof the present invention exhibit a higher quantum yield as compared withthe wavelength conversion luminescent resin compositions (wavelengthconversion members) of Comparative Examples.

What is claimed is:
 1. A wavelength conversion luminescent resincomposition, comprising: at least one compound represented by Formula(1); and a resin,

in Formula (1), Y¹ and Y² each independently represent a halogen atom,an alkyl group, an aryl group, a hydroxy group, an alkoxy group, or anaryloxy group, each of which may have a substituent, and Y¹ and Y² maybe linked to each other to form a ring; R³ represents a hydrogen atom,an alkyl group, an aryl group, a heterocyclic group, an ethenyl group,an ethynyl group, or an acyl group, each of which may have asubstituent; Ar³ and Ar⁴ each independently represent an aryl group,each of which may have a substituent; and R⁴ to R¹¹ each independentlyrepresent a hydrogen atom, a halogen atom, an alkyl group, an arylgroup, a heterocyclic group, an ethenyl group, an ethynyl group, an acylgroup, an alkoxy group, an aryloxy group, an alkylthio group, anarylthio group, or an amino group, each of which may have a substituent,and at least one of R⁴, . . . , or R¹¹ represents a substituentrepresented by Formula (2) or Formula (3),

in Formula (2), R²⁰¹ represents a halogen atom, an alkyl group, an arylgroup, a heterocyclic group, an ethenyl group, an ethynyl group, an acylgroup, a silyl group, an alkoxy group, an aryloxy group, an alkylthiogroup, an arylthio group, or an amino group, each of which may have asubstituent; and Q represents an aromatic ring which may have asubstituent,

in Formula (3), R¹⁰¹ represents an alkyl group, an aryl group, aheterocyclic group, an ethenyl group, an ethynyl group, or an acylgroup, each of which may have a substituent; Ar¹⁰¹ represents an arylgroup or a heterocyclic group, each of which may have a substituent; andAr¹⁰¹ and R²⁰¹ may be linked to each other to form a ring.
 2. Thewavelength conversion luminescent resin composition according to claim1, wherein at least one of R⁴, . . . , or R¹¹ represents a substituentrepresented by Formula (5),

in Formula (5), R²⁰¹ to R²⁰⁵ each represent a hydrogen atom, a halogenatom, an alkyl group, an aryl group, a heterocyclic group, an ethenylgroup, an ethynyl group, an acyl group, a silyl group, an alkoxy group,an aryloxy group, an alkylthio group, an arylthio group, or an aminogroup, and at least one of R²⁰¹ or R²⁰⁵ is a group other than a hydrogenatom; and R²⁰¹ and R²⁰² may be linked to each other to form a ring, R²⁰²and R²⁰³ may be linked to each other to form a ring, R²⁰³ and R²⁰⁴ maybe linked to each other to form a ring, and R²⁰⁴ and R²⁰⁵ may be linkedto each other to form a ring.
 3. The wavelength conversion luminescentresin composition according to claim 1, wherein Ar³ and Ar⁴ are eachindependently a substituent represented by Formula (2),

in Formula (2), R²⁰¹ represents a halogen atom, an alkyl group, an arylgroup, a heterocyclic group, an ethenyl group, an ethynyl group, an acylgroup, a silyl group, an alkoxy group, an aryloxy group, an alkylthiogroup, an arylthio group, or an amino group, each of which may have asubstituent; and Q represents an aromatic ring which may have asubstituent.
 4. The wavelength conversion luminescent resin compositionaccording to claim 1, wherein Ar³ and Ar⁴ are each independently asubstituent represented by Formula (5),

in Formula (5), R²⁰¹ to R²⁰⁵ each represent a hydrogen atom, a halogenatom, an alkyl group, an aryl group, a heterocyclic group, an ethenylgroup, an ethynyl group, an acyl group, a silyl group, an alkoxy group,an aryloxy group, an alkylthio group, an arylthio group, or an aminogroup, and at least one of R²⁰¹ or R²⁰⁵ is a group other than a hydrogenatom; and R²⁰¹ and R²⁰² may be linked to each other to form a ring, R²⁰²and R²⁰³ may be linked to each other to form a ring, R²⁰³ and R²⁴ may belinked to each other to form a ring, and R²⁰⁴ and R²⁰⁵ may be linked toeach other to form a ring.
 5. A wavelength conversion member comprisingthe wavelength conversion luminescent resin composition according toclaim
 1. 6. A light-emitting element comprising the wavelengthconversion member according to claim
 5. 7. A method for producing awavelength conversion luminescent resin composition, comprising: a stepof drying a solution containing at least one compound represented byFormula (1) and a resin in a solvent,

in Formula (1), Y¹ and Y² each independently represent a halogen atom,an alkyl group, an aryl group, a hydroxy group, an alkoxy group, or anaryloxy group, each of which may have a substituent, and Y¹ and Y² maybe linked to each other to form a ring; R³ represents a hydrogen atom,an alkyl group, an aryl group, a heterocyclic group, an ethenyl group,an ethynyl group, or an acyl group, each of which may have asubstituent; Ar³ and Ar⁴ each independently represent an aryl group,each of which may have a substituent; and R⁴ to R¹¹ each independentlyrepresent a hydrogen atom, a halogen atom, an alkyl group, an arylgroup, a heterocyclic group, an ethenyl group, an ethynyl group, an acylgroup, an alkoxy group, an aryloxy group, an alkylthio group, anarylthio group, or an amino group, each of which may have a substituent,and at least one of R⁴, . . . , or R¹¹ represents a substituentrepresented by Formula (2) or Formula (3),

in Formula (2), R²⁰¹ represents a halogen atom, an alkyl group, an arylgroup, a heterocyclic group, an ethenyl group, an ethynyl group, an acylgroup, a silyl group, an alkoxy group, an aryloxy group, an alkylthiogroup, an arylthio group, or an amino group, each of which may have asubstituent; and Q represents an aromatic ring which may have asubstituent,

in Formula (3), R¹⁰¹ represents an alkyl group, an aryl group, aheterocyclic group, an ethenyl group, an ethynyl group, or an acylgroup, each of which may have a substituent; Ar¹⁰¹ represents an arylgroup or a heterocyclic group, each of which may have a substituent; andAr¹⁰¹ and R²⁰¹ may be linked to each other to form a ring.
 8. A methodfor producing a wavelength conversion luminescent resin composition,comprising: a step of curing a composition containing at least onecompound represented by Formula (1) and a monomer and/or apolymerization precursor,

in Formula (1), Y¹ and Y² each independently represent a halogen atom,an alkyl group, an aryl group, a hydroxy group, an alkoxy group, or anaryloxy group, each of which may have a substituent, and Y¹ and Y² maybe linked to each other to form a ring; R³ represents a hydrogen atom,an alkyl group, an aryl group, a heterocyclic group, an ethenyl group,an ethynyl group, or an acyl group, each of which may have asubstituent; Ar³ and Ar⁴ each independently represent an aryl group,each of which may have a substituent; and R⁴ to R¹¹ each independentlyrepresent a hydrogen atom, a halogen atom, an alkyl group, an arylgroup, a heterocyclic group, an ethenyl group, an ethynyl group, an acylgroup, an alkoxy group, an aryloxy group, an alkylthio group, anarylthio group, or an amino group, each of which may have a substituent,and at least one of R⁴, . . . , or R¹¹ represents a substituentrepresented by Formula (2) or Formula (3),

in Formula (2), R²⁰¹ represents a halogen atom, an alkyl group, an arylgroup, a heterocyclic group, an ethenyl group, an ethynyl group, an acylgroup, a silyl group, an alkoxy group, an aryloxy group, an alkylthiogroup, an arylthio group, or an amino group, each of which may have asubstituent; and Q represents an aromatic ring which may have asubstituent,

in Formula (3), R¹⁰¹ represents an alkyl group, an aryl group, aheterocyclic group, an ethenyl group, an ethynyl group, or an acylgroup, each of which may have a substituent; Ar¹⁰¹ represents an arylgroup or a heterocyclic group, each of which may have a substituent; andAr¹⁰¹ and R²⁰¹ may be linked to each other to form a ring.
 9. A methodfor producing a wavelength conversion luminescent resin composition,comprising: a step of melting a composition containing at least onecompound represented by Formula (1) and a resin,

in Formula (1), Y¹ and Y² each independently represent a halogen atom,an alkyl group, an aryl group, a hydroxy group, an alkoxy group, or anaryloxy group, each of which may have a substituent, and Y¹ and Y² maybe linked to each other to form a ring; R³ represents a hydrogen atom,an alkyl group, an aryl group, a heterocyclic group, an ethenyl group,an ethynyl group, or an acyl group, each of which may have asubstituent; Ar³ and Ar⁴ each independently represent an aryl group,each of which may have a substituent; and R⁴ to R¹¹ each independentlyrepresent a hydrogen atom, a halogen atom, an alkyl group, an arylgroup, a heterocyclic group, an ethenyl group, an ethynyl group, an acylgroup, an alkoxy group, an aryloxy group, an alkylthio group, anarylthio group, or an amino group, each of which may have a substituent,and at least one of R⁴, . . . , or R¹¹ represents a substituentrepresented by Formula (2) or Formula (3),

in Formula (2), R²⁰¹ represents a halogen atom, an alkyl group, an arylgroup, a heterocyclic group, an ethenyl group, an ethynyl group, an acylgroup, a silyl group, an alkoxy group, an aryloxy group, an alkylthiogroup, an arylthio group, or an amino group, each of which may have asubstituent; and Q represents an aromatic ring which may have asubstituent,

in Formula (3), R¹⁰¹ represents an alkyl group, an aryl group, aheterocyclic group, an ethenyl group, an ethynyl group, or an acylgroup, each of which may have a substituent; Ar¹⁰¹ represents an arylgroup or a heterocyclic group, each of which may have a substituent; andAr¹⁰¹ and R²⁰¹ may be linked to each other to form a ring.